Clearly, that release is generally the trickiest part of the whole show. But since you retain the option of simply snipping the leader, it shouldn't be difficult. Our fish seemed in good shape at kayak-side; we had to tow a couple for 10 to 15 minutes before they began to kick too strongly to hold.
Hobie does make livewells for its kayaks, as do other manufacturers (such as Shimano). They work great but add a bit of weight/space some anglers prefer to avoid when they can. Acceding just in this small way that bit of independence, I relied on a VHF call to the tender to run over to me another livey (or sweet-talked one out of one of the boats on the bank, if nearby.)
7. Who shouldn't try this?
Anyone not in reasonably good shape - there's definitely no need to be an athlete, but you'll need some endurance for fighting stripes from a kayak. (I caught two one day; my next goal is four - that's far from impossible or even improbable, but it takes some effort.) Anyone who has an active daredevil streak or has a hard time using common sense would be better off fishing from a cockpit. Anyone without some sense of adventure might want to fish Cabo more conventionally.
8. What should I bring?
Marlin Masters provides good tackle - TLD 25s and Penn Baja Specials on Melton 30-pound pitch-bait rods with 50-pound braid under a 40-pound mono top shot. Still, I brought my own Shimano Torsa 20 with 50-pound braid and found that smaller, lighter outfit to be ideal. I matched that to a 7-foot Tallus rod. I recommend a rod of that length; anything shorter makes it difficult to work the rod from side to side around the bow, something you'll need to do very often during the fight.
No special outerwear is required, though on one chilly morning I was glad I'd brought some kayak bibs with booties (Kokatat Watersports Wear; www.kokatat.com), which also makes a great ultra-lightweight windbreaker. Most of the time, whatever you'd wear in the cockpit of a boat works fine. Most kayak anglers bring a pair of wading or kayak booties (though I prefer the barefoot approach myself on warmer days). I'd also recommend a couple of good dry bags and some various bungee cords, useful in so many ways.
9. When should I go?
Anytime of the year with good weather offers worthwhile kayak fishing offshore. Marlin are always a possibility, as are dorado, yellowfin and wahoo. If stripes are your goal, mid-September into January is your time; then the banks are loaded with life, including many pods of marlin. (Early in that period the marlin tend to be a bit farther north, over the Finger Banks; by October, they're usually moving to the closer Golden Gate.) You don't even have to travel out to the offshore banks to get pelagics from a yak: Wahoo, dorado and skipjack can be caught barely off the arch (tip of Cabo), along with various nearshore predators.
It's worth reiterating that hooking striped marlin from a kayak is not for everyone. But for anglers seeking one of fishing's ultimate challenges, it's a thrill ride like nothing else in the world.